C18-Ceramide-d - ≥99% , CAS No.1840942-14-4

CAS: 1840942-14-4 Cat. No.: C1440123 Formula: C₃₆H₆₄D₇NO₃ Molecular Weight: 573.00

GRADE & PURITY ≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

C18-Ceramide-d 7 is deuterium labeled C18-Ceramide.

Specifications

Specifications & Purity

≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

Molecular Weight

573.00

Application Protocols

The following are general, literature‑based protocols suitable for ceramides and deuterated analogs; adapt to your system. They are not item‑specific validated methods.

1. Preparation of stock solutions

• Weigh under inert gas if possible. Dissolve to 5–10 mg/mL in DMSO, ethanol, or hot isopropanol (40–60 °C). Sonicate in a water bath until clear. Aliquot into amber vials, purge with N2/Ar, cap tightly.

2. Lipid film hydration for vesicles

• Dissolve ceramide (and co‑lipids, e.g., POPC/cholesterol) in CHCl3/MeOH (2:1). Evaporate to a thin film under N2, then vacuum‑dry ≥1 h. Hydrate with HEPES buffer (10 mM HEPES, 150 mM NaCl, pH 7.4) at 60 °C with vortex/sonication. Optional: extrude through 100 nm membranes. Note: high ceramide fractions can increase Tm; hydrate above phase transition.

3. BSA complexation for aqueous delivery

• Prepare 10% (w/v) fatty acid‑free BSA in PBS (37–50 °C). Add a warm ceramide stock in ethanol or DMSO dropwise with vigorous stirring to reach desired molar ratio (e.g., lipid:BSA 2:1 to 6:1). Mix 30–60 min at 37 °C.

4. LC–MS/MS internal standard use

• Spike a fixed amount of deuterated ceramide into samples before extraction. Extract with IPA/ACN/H2O (2:1:1). Analyze in positive ESI MRM monitoring [M+H]+ and characteristic neutral loss (e.g., 264 for sphingoid base, method‑dependent). Construct calibration curves with matrix‑matched standards.

Always verify instrument and assay compatibility with small‑scale pilots.

Biological Roles

Content in this section reflects general ceramide biochemistry; it does not describe clinical uses.

• Core role in sphingolipid metabolism (literature)

  • Ceramide is the central hub of sphingolipid pathways, generated from de novo synthesis (serine + palmitoyl‑CoA → sphinganine → N‑acylation → dihydroceramide → desaturation) or via salvage from complex sphingolipids.
  • Chain length specificity (e.g., C18) can influence biophysical membrane properties and protein interactions.

• Signaling and regulation (literature/general)

  • Ceramides modulate membrane microdomain organization, affecting receptor clustering and downstream signaling cascades.
  • They can influence protein phosphatases (e.g., PP2A) and kinases indirectly through membrane effects and ceramide‑activated factors in cell‑free systems.

• Biophysical characteristics

  • Strong gel‑phase promoter in model membranes; elevates bilayer order and can drive lateral segregation with cholesterol and saturated phospholipids.

• Isotopic labeling utility

  • Deuterated ceramides are valuable in mass‑spectrometry‑based flux analysis and in neutron/NMR studies where isotopic contrast or peak separation is desired.

Note: Any experimental work using this item should be framed as research only (per Product Data). No medical or therapeutic claims are made or implied.

Buffer Applications

Ceramides are not classical buffering agents and do not establish defined pH ranges. Consequently, this section is not typically applicable.

Practical notes (general)

• Disperse ceramides into buffers using carriers (fatty acid‑free BSA, mild non‑ionic detergents) or through liposome formation. Adjusting pH may influence headgroup ionization of co‑lipids but has negligible effect on the non‑ionizable ceramide amide/alkyl chains.
• Common dispersion buffers: HEPES‑ or PBS‑based systems with 0.1–2% BSA or 0.05–0.5% Tween‑20/Triton X‑100, as allowed by the assay.

Green Alternatives

Handling of ceramides often involves chlorinated solvents (chloroform, DCM) due to powerful solvency. Where possible, consider greener choices recognizing trade‑offs.

Greener solvent substitutions (literature/general)

• Replace CHCl3 with isopropanol or ethanol (hot) for dissolution; for film formation, tert‑butanol can be lyophilized to leave uniform films without chlorinated waste.
• Analytical extraction: use IPA/ACN/H2O (2:1:1) in lipidomics workflows instead of Bligh–Dyer (CHCl3/MeOH) when method sensitivity allows.
• Use cyclopentyl methyl ether (CPME) or 2‑MeTHF for certain synthetic manipulations of sphingoid intermediates instead of DCM/THF.

Comparison (general trends)

• Chloroform: excellent solubility, non‑green, toxic, halogenated waste.
• Isopropanol (hot): good solubility, safer, higher bp may require heating.
• Ethanol: safer, sometimes insufficient at room temperature.
• ACN/IPA/water mixes: LC–MS compatible, greener profile, may extract different lipid subsets.

Trade‑offs and mitigation

• Heating/sonication needed for green alcohols; ensure closed containers to limit vapor exposure.
• For quantitative work, verify recovery and response factors after changing solvent systems.
• Waste minimization: scale dissolutions appropriately and reuse dedicated glassware to reduce solvent rinses.

Pharmaceutical Uses

No pharmacopeial grade or excipient designation is provided for this item; it is labeled for research use only.

General context (non‑clinical)

• Ceramides can be components of experimental lipid formulations (e.g., liposomes, solid‑lipid particles) for physicochemical studies of membrane stability, permeability, or cargo release. Deuterated variants assist with tracing distribution and stability in preclinical analytical assays.
• In topical and cosmetic science, ceramide analogs are studied for barrier function in model systems; however, this product is not offered for cosmetic or clinical use.

Formulation considerations (general)

• Solubilization: employ co‑solvents (ethanol/IPA) or warm dispersion into phospholipid matrices; melt‑blend with saturated phospholipids to increase incorporation.
• Analytical control: include stable‑isotope internal standards (as provided by deuterated species) for mass balance and degradation tracking.

Compliance note

• For any cGMP or clinical applications, source appropriate grade and documentation. This catalog item lacks such designation; refer to CoA/Spec Sheet for all available quality attributes.

Physical Properties

Item-specific physicochemical specifications are not provided in the Product Data and should be confirmed on the CoA/Spec Sheet.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point (literature, typical C18 ceramides): often in the 85–105 °C range, depending on sphingoid base saturation and isotopic labeling. Deuteration can shift Tm slightly upward relative to protiated analogs.
• Density: not widely reported for individual ceramides; typically near 0.9–1.0 g/mL (literature estimate for waxy long‑chain lipids). Use as qualitative guidance only.
• Solubility (literature/general)
  • Water: practically insoluble.
  • Organic: soluble in chloroform, dichloromethane, 2:1 CHCl3/MeOH, hot ethanol/isopropanol; sparingly soluble in DMSO at room temperature but forms clear stocks at elevated temperature with sonication.
• Partitioning (literature/general): extremely hydrophobic; very high logP expected for C18 ceramides (>8). Exact value depends on sphingoid base and labeling.
• Refractive index: not typically reported for solids of this class.
• pKa: amide is non‑basic under physiological conditions; terminal hydroxyl pKa ~15–16 (aliphatic alcohol, literature), not titratable in aqueous buffers.

Notes

• Provide temperature‑assisted dissolution (40–60 °C) and/or bath sonication to prepare concentrated stocks.
• For analytical work (LC–MS), use anhydrous solvents; add 0.1% formic acid or 5 mM ammonium formate as mobile‑phase modifiers as per method development (literature practice).

Quality & Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting typical lipid standards’ grades (general)

• Analytical/LC–MS grade lipids: manufactured to minimize peroxides, short‑chain impurities, and isobaric contaminants; come with assay by HPLC/UPLC and detailed isotopic enrichment for deuterated species.
• Research grade: suitable for most biochemical and biophysical experiments; may have broader limits on minor homologs or positional isomers.
• Isotopic labeling quality: for “‑d” ceramides, critical quality attributes include total deuterium count, labeling positions, isotopic enrichment (>98 atom % D is common in high‑grade materials), and residual protiated fraction—verify on CoA.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. Many lipid standards are shipped without stabilizers but packed under inert gas.

What to check on receipt

• CoA metrics: assay (%), isomeric purity (d18:1 vs d18:0 if relevant), water content, peroxide value (if provided), isotopic enrichment, residual solvents.
• Visual: ensure no discoloration; off‑white to pale solid is typical for many ceramides, but appearance for this item is not specified.
• Analytical confirmation: quick LC–MS/MS check against expected m/z for the labeled species enhances traceability for quantitative workflows.

Reaction & Applications

This product is primarily a labeled lipid standard or research reagent rather than a synthetic intermediate; however, C18‑ceramides (including deuterated analogs) are widely used in:

• Lipidomics and quantitation (general/literature)

  • As internal standards for LC–MS/MS quantitation of endogenous ceramides, enabling correction for extraction and ionization variability via stable‑isotope dilution.
  • Benchmarking chromatographic separations of chain length/saturation isomers.

• Biophysical studies

  • Model membranes: incorporation into lipid bilayers to examine phase behavior, domain formation, and permeability; deuteration facilitates neutron scattering or NMR contrast.

• Enzymology and metabolism

  • Substrates or tracers for ceramidases, sphingomyelin synthases, and glycosyltransferases in cell‑free systems; mass shifts enable flux analysis.

Practical tips (general)

• Minimize oxidation: especially if the sphingoid base contains a double bond (d18:1). Work under argon/nitrogen; add trace antioxidants (e.g., 50 µM BHT) if compatible with downstream analytics.
• Accurate dosing: prepare concentrated stocks, warm and vortex thoroughly, then make serial dilutions immediately before use.
• Adsorption losses: pre‑rinse glassware/syringes with a small volume of the ceramide solution before preparing standards to reduce wall losses.
• LC–MS ionization: ceramides ionize well in positive ESI as [M+H]+ and [M+H–H2O]+; in negative ESI as [M–H]− (literature). Optimize source temperature to avoid thermal decomposition.

Reaction Conditions

General literature conditions relevant to ceramide transformations and handling (not item‑specific):

• Glycosylation to glycosphingolipids

  • Donors: per‑acetylated glycosyl trichloroacetimidates or thioglycosides.
  • Activators: TMSOTf (0.05–0.2 equiv) or NIS/TfOH at −78 to −20 °C in dry DCM/Et2O; 1–4 h typical. Yields commonly 50–85% depending on donor/acceptor match and protection.

• Phosphocholine installation (sphingomyelin analogs)

  • Reagents: CDI‑activated phosphocholine or POCl3‑derived chlorophosphates; base (DIPEA), dry CH2Cl2/DMF, 0–25 °C, 2–16 h; 40–70% typical.

• Amide manipulations (when starting from sphingoid base)

  • Fatty acid coupling: EDC·HCl/HOBt or HATU with DIPEA in DCM/DMF, 0–25 °C, 2–12 h; 60–90% literature yields. For isotopic integrity, avoid protic acids that could promote exchange at labeled positions (if allylic/benzylic D present in a specific design).

• Hydrogenation/desaturation adjustments

  • Pd/C hydrogenation (H2, 1–3 atm, EtOH/EtOAc, rt–40 °C) to convert d18:1 to d18:0 derivatives; monitor to prevent over‑reduction of sensitive labels (not generally an issue for C–D bonds at aliphatic positions).

• Workup/handling

  • Maintain anhydrous conditions; adsorptive losses to silica/glass are significant—pre‑wet with eluent or add 0.1% Et3N to reduce tailing during chromatography.

All temperature, time, and yield values are literature guidance and should be optimized experimentally for the specific ceramide and labeling pattern.

Safety & Handling

Safety information specific to this catalog item is not supplied in the Product Data. Always consult the SDS for authoritative guidance.

• GHS classification, signal word, pictograms, H‑statements: Not specified for this item; refer to SDS.
• Likely hazards (general for long‑chain lipids): low volatility; dust may be irritating to eyes/respiratory tract if powdered. Not expected to be acutely toxic by dermal contact, but avoid exposure.

Handling recommendations (general best practice)

• PPE: lab coat, nitrile gloves, safety glasses. Use a dust mask if handling powders prone to aerosolization.
• Engineering controls: handle in a clean, dry area. Use a fume hood for weighing/dissolution to avoid aerosol and solvent exposure.
• Incompatibilities: strong oxidizers; avoid excessive heat and prolonged light exposure which may promote oxidation of unsaturations (if present).
• Spill/accidental release: collect solids with disposable spatula, wipe residues with organic solvent (e.g., isopropanol or DCM) and absorbent; dispose per institutional procedures.
• First aid (general):
  • Inhalation: move to fresh air; seek medical advice if symptoms persist.
  • Skin: wash with soap/water; remove contaminated clothing.
  • Eyes: rinse cautiously with water for several minutes; remove contacts if present and easy to do; seek medical attention if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

Additional notes

• For LC–MS/isotope‑tracer work, minimize cross‑contamination by dedicating glassware and avoiding plasticizers.
• Research use only (per Product Data).

Solvent Selection

C18‑ceramides are highly hydrophobic amphiphiles with poor aqueous solubility. Solvent choice dictates successful dissolution, delivery, and analytical performance.

• Miscibility/solubility profile (literature/general)

  • Good: chloroform, dichloromethane, 2:1 CHCl3/MeOH, methanol (hot), isopropanol (hot), hexane (limited but useful for TLC), toluene (hot), THF.
  • Moderate: DMSO (room temperature to warm), DMF (warm).
  • Poor: water, aqueous buffers without carriers.

• Practical recommendations

  • Stock solutions for biochemistry: 1–10 mg/mL in DMSO, ethanol, or isopropanol; warm to 40–60 °C with gentle bath sonication until clear, then aliquot.
  • Lipid film method: dissolve in CHCl3/MeOH (2:1), dry to a thin film, then hydrate with buffer containing a carrier (e.g., 0.1–2% fatty acid‑free BSA) or with detergent; sonicate or extrude to disperse.
  • LC–MS sample prep: dissolve in CHCl3/MeOH/isopropanol; switch to MeOH/IPA/ACN mobile‑phase compatible mixtures prior to analysis.

• When to choose alternatives

  • If avoiding chlorinated solvents, hot isopropanol or tert‑butanol/water (for liposomes) can be effective.
  • For cell‑free enzyme assays, DMSO or ethanol stocks diluted to ≤1% v/v final often balance solubility with assay tolerance.

• Compatibility

  • Avoid prolonged contact with polystyrene or PVC; use glass or solvent‑resistant plastics (PP, PTFE).

Storage & Reconstitution

• Storage conditions (item-specific)

  • Store at −20 °C (per Product Data). Keep tightly closed in the original container.
  • Shipped in an ice chest with ice pads (per Product Data). Upon receipt, return to −20 °C promptly.

• Additional best practices (general for lipids)

  • Protect from light and moisture. Purge headspace with dry nitrogen or argon after each use to limit oxidation and hydrolysis.
  • If available as a film or solid, consider storing as pre‑weighed single‑use aliquots to avoid repeated warming/cooling.
  • For long‑term storage (>6 months), −20 °C to −80 °C is typical for ceramides; verify stability on CoA. Avoid frost‑free freezers that cycle temperature.

• Reconstitution

  • Warm to room temperature (or 40–60 °C if needed) before opening to minimize condensation. Dissolve in a suitable solvent (e.g., DMSO, ethanol, isopropanol, or CHCl3/MeOH 2:1) with gentle bath sonication until clear.
  • Prepare aliquots of working solutions, cap tightly, and store at −20 °C. Minimize freeze–thaw cycles; discard aliquots showing precipitation, turbidity, or discoloration.

• Stability/quality checks

  • Periodically confirm integrity by LC–MS (expected m/z for deuterated analog) and by TLC (single major spot). Any item‑specific stability statements: Not specified for this item; refer to CoA/Spec Sheet.

• Research use only (per Product Data).

Structure & Identity

C18‑Ceramide‑d is described as a C18-chain ceramide, commonly referring to an N‑stearoyl (18:0) amide of a long‑chain sphingoid base; the suffix “‑d” typically denotes a deuterium‑labeled variant used for isotope‑tracing or internal standard work.

• Item-specific identifiers

  • CAS: 1840942-14-4
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general/literature for C18 ceramides and deuterated analogs)

  • Core: ceramide = sphingoid base (typically d18:1 or d18:0) bearing an amide linkage to a C18 fatty acid (stearic, 18:0).
  • Functional groups: primary amide (–CONH–), secondary alcohol (C1‑OH), often a trans double bond at C4–C5 in d18:1 sphingosine; fully saturated for dihydro series (d18:0).
  • Isotopic labeling: “‑d” indicates incorporation of deuterium at defined positions (supplier‑specific); positions and D count are item‑specific and should be confirmed on the CoA.
  • Stereochemistry: natural ceramides are typically 2S,3R in the sphingoid base; exact configuration for this catalog item is not specified.

• 2D description in words (general)

  • A long, mostly saturated hydrocarbon chain (C18 acyl) linked via an amide to a long‑chain amino alcohol (sphingoid base), which bears a second long hydrocarbon segment and at least one hydroxyl. The molecule is amphiphilic but strongly hydrophobic, with the polar amide and hydroxyls clustered near the midpoint of two long aliphatic segments.

Synthetic Utility

Although sold primarily as a research reagent/standard, ceramide frameworks are valuable synthetic intermediates in sphingolipid chemistry (literature/general):

• Upstream/downstream conversions

  • Glycosylation of ceramide → glycosphingolipids (e.g., glucosylceramide, galactosylceramide) under neighboring‑group‑controlled glycosyl donors (e.g., trichloroacetimidates) with Lewis acids (TMSOTf) at low temperature.
  • Phosphorylcholine transfer → sphingomyelin analogs via activated phosphocholine donors.
  • Oxidation/reduction at C3 or C4 of the sphingoid base to access varied sphingoid motifs (e.g., phytoceramides).

• Protection strategies

  • Temporary protection of the C1‑OH as benzyl or silyl ether to direct site‑selective transformations; amide N often left unprotected due to low nucleophilicity.

• Isotopic considerations

  • With deuterated substrates, maintain labeling by avoiding exchangeable D at heteroatom‑bound positions; deuteriums on carbon are stable, but harsh acid/base or metal hydride conditions could scramble labeling at benzylic/allylic positions of model systems.

• Analytical leverage

  • Use the labeled ceramide as an internal standard to quantify yields and recovery of synthetic transformations of unlabeled sphingolipids via LC–MS/MS.

Note: The exact reactivity and conditions depend on whether the sphingoid base is d18:1 vs d18:0 and on the labeling pattern; consult primary literature when planning synthesis.

Target Specificity

This product is a small‑molecule lipid, not a biological affinity reagent. There is no antigen/epitope or species reactivity associated with this item.

• Target specificity: Not applicable.
• Tested reactivity, clone/isotype: Not applicable.

For functional studies, specificity relates to biochemical pathways (e.g., sphingolipid enzymes) rather than immunochemical targets; see “Biological Roles” and “Reaction & Applications.”

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 1840942-14-4, the molecular formula is C36H64D7NO3, and the molecular weight is 573.00 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.